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Kristine - I so agree about pairing a matched set with a neutral top as a "statement in itself" - that is a great idea, and super fun, if done with a nod to the 40s/50s.
ticksgirl - I highly recommend tissues in the sleeve for a toddler's cold. Saved me lots of time scrambling in the diaper bag. Sometimes being a mom is just not fashionable.
AG: I wouldn't do it with costume jewelry, but I occasionally match high-end jewelry. I don't think it looks old fashioned when matched with the right outfit. I found that I like some of my jewelry matched especially with evening wear and color-blocked outfits. But I'm Turkish and jewelry is gifted a lot in our culture, generally in sets. So I won a few all-matched sets and mostly break them up.